Potassium Phosphate, Tribasic → 6-(4-(2-Methoxy-ethoxymethoxy)-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of 6-chloro-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (5.9 g), 4-(2-methoxy-ethoxymethoxy)-3-trifluoromethyl-phenyl-boronic acid (9.92 g), potassium phosphate (11.1 g), tris(dibenzylideneacetone)dipalladium (1.4 g) and tricyclohexylphosphine (1.03 g) in dioxane (190 ml) and water (60 ml) was heated at 100° C. under nitrogen atmosphere for 2 hours. After cooling to room temperature, the mixture was then extracted with ethyl acetate (500 ml×2), the combined organic layers were dried over sodium sulphate and solvent was then removed under reduced pressure. To the residue was then added methanol (20 ml), and the solid product, 6-(4-(2-methoxy-ethoxymethoxy)-3-trifluoromethyl-phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile was collected by filtration (8.95 g). 1H NMR (CDCl3) δ: 8.27 (m, 1H), 8.19 (m, 1H), 8.10 (s, 1H), 7.88 (s, 1H), 7.42 (m, 1H), 5.44 (s, 2H), 3.99 (s, 3H), 3.88 (m, 2H), 3.58 (m, 2H), 3.38 (s, 3H). MS m/z 407 (M+1).

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